4-Chloro-N′-[(Z)-4-nitro­benzyl­idene]benzohydrazide monohydrate

Fun, H.-K.; Patil, P.S.; Rao, J.N.; Kalluraya, B.; Chantrapromma, S.

doi:10.1107/S160053680802446X

organic compounds

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ISSN: 2056-9890

Volume 64| Part 9| September 2008| Page o1707

doi:10.1107/S160053680802446X

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4-Chloro-N′-[(Z)-4-nitrobenzylidene]benzohydrazide monohydrate

Hoong-Kun Fun,^a ^* P. S. Patil,^b Jyothi N. Rao,^c B. Kalluraya ^c and Suchada Chantrapromma ^d ‡

^aX-ray Crystallography Unit, School of Physics, Universiti Sains Malaysia, 11800 USM, Penang, Malaysia, ^bDepartment of Studies in Physics, Mangalore University, Mangalagangotri, Mangalore 574 199, India, ^cDepartment of Studies in Chemistry, Mangalore University, Mangalagangotri, Mangalore 574 199, India, and ^dCrystal Materials Research Unit, Department of Chemistry, Faculty of Science, Prince of Songkla University, Hat-Yai, Songkhla 90112, Thailand
^*Correspondence e-mail: hkfun@usm.my

(Received 16 July 2008; accepted 31 July 2008; online 6 August 2008)

In the title compound, C₁₄H₁₀ClN₃O₃·H₂O, the benzohydrazide group is not planar and the molecule exists in a cis configuration with respect to the methylidene unit. The dihedral angle between the two substituted benzene rings is 38.7 (3)°. In the crystal structure, molecules are linked by O—H⋯O, O—H⋯N and N—H⋯O hydrogen bonds into a two-dimensional network parallel to the (100) plane. The crystal structure is further stabilized by weak C—H⋯O interactions.

Related literature

For bond-length data, see: Allen et al. (1987 ). For background to the activities of hydrazones, see, for example: Bedia et al. (2006 ); Rollas & Kouçoukgouzel (2007 ).

Experimental

Crystal data

C₁₄H₁₀ClN₃O₃·H₂O
M_r = 321.72
Monoclinic, P 2₁ /c
a = 16.3049 (8) Å
b = 6.8783 (4) Å
c = 12.7209 (7) Å
β = 104.122 (4)°
V = 1383.53 (13) Å³
Z = 4
Mo Kα radiation
μ = 0.30 mm⁻¹
T = 100.0 (1) K
0.38 × 0.21 × 0.10 mm

Data collection

Bruker SMART APEX2 CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2005 ) T_min = 0.896, T_max = 0.971
14031 measured reflections
3172 independent reflections
2558 reflections with I > 2σ(I)
R_int = 0.044

Refinement

R[F² > 2σ(F²)] = 0.086
wR(F²) = 0.239
S = 1.13
3172 reflections
199 parameters
H-atom parameters constrained
Δρ_max = 1.40 e Å⁻³
Δρ_min = −0.46 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1W—H1W⋯O3ⁱ	0.88	1.93	2.794 (5)	168
O1W—H2W⋯O3ⁱⁱ	0.89	2.29	2.898 (5)	126
O1W—H2W⋯N2ⁱⁱ	0.89	2.32	3.185 (5)	163
N1—H1N1⋯O1W	0.85	2.04	2.818 (5)	151
C2—H2A⋯O1ⁱⁱⁱ	0.93	2.40	3.329 (6)	176
C14—H14A⋯O1W^iv	0.93	2.51	3.322 (6)	146
Symmetry codes: (i) $[-x+1, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]$ ; (ii) $[x, -y+{\script{3\over 2}}, z+{\script{1\over 2}}]$ ; (iii) $[x+1, -y+{\script{3\over 2}}, z+{\script{1\over 2}}]$ ; (iv) $[x, -y+{\script{3\over 2}}, z-{\script{1\over 2}}]$ .

Data collection: APEX2 (Bruker, 2005); cell refinement: APEX2; data reduction: SAINT (Bruker, 2005); program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2003 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S160053680802446X/hb2764sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S160053680802446X/hb2764Isup2.hkl

checkCIF report

Comment top

Hydrazones have been demonstrated to possess antimicrobial, anticonvulsant, analgesic, antiinflammatory, antiplatelet, antitubercular, anticancer and antitumor activities (e.g. Bedia et al., 2006). Hydrazones possessing an azometine –NHN=CH– proton constitute an important class of compounds for new drug development. Many researchers have therefore synthesized these compounds as target structures and evaluated their biological activities. These observations have served as guides for the development of new hydrazones that possess varied biological activities. These compounds are synthesized by heating the appropriate substituted hydrazines/hydrazides with aldehydes and ketones in solvents like ethanol, methanol, tetrahydrofuran, butanol, glacial acetic acid, ethanol-glacial and acetic acid. Another synthetic route for the synthesis of hydrazones is the coupling of aryldiazonium salts with active hydrogen compounds (Rollas & Kοuçοukgοuzel, 2007).

In the structure of the title compound (I) (Fig. 1), the molecule exist in a cis-configuration with respect to the methylidene unit (C8=N2). The dihedral angle between the two substituted benzene rings is 38.7 (3)°. In the 4-nitrophenyl unit, the nitro group is slightly twisted from the mean plane of the C9–C14 ring with the torsion angles O1–N3–C12–C13 = 174.9 (5)° and O2–N3–C12–C13 = -4.4 (8)°. The benzohydrazide moiety (N1/N2/O3/C1–C7) is not planar as indicated by the interplanar angle between the N1/N2/O3/C7 plane and C1–C6 pheny ring of 17.2 (3)°. The mean plane through N1/N2/C8/C9 plane makes the dihedral angle of 9.1 (5)° with the N1/N2/O3/C7 plane. The orientation of the benzohydrazide with respect to methylidine unit can be indicated by the torsion C7–N1–N2–C8 of 174.0 (5)°. The bond distances and angles are in normal ranges (Allen et al., 1987).

The water molecule is involved in O—H···O, O—H···N and N—H···O hydrogen bonds (Table 1). These hydrogen bonds linked the molecules into two dimensional networks parallel to the (100) plane as shown in Fig. 2. The crystal is further stabilized by weak C—H···O interactions (Table 1).

Related literature top

For bond-length data, see: Allen et al. (1987). For background to the activities of hydrazones, see, for example: Bedia et al. (2006); Rollas & Kοuçοukgοuzel (2007).

Experimental top

The title compound was prepared by refluxing 4-chlorophenyl hydrazide (0.01 mol), 4-nitro benzaldehyde (0.01 mol) in ethanol (30 ml) and 3 drops of concentrated sulfuric acid for 3 hrs. Excess ethanol was removed from the reaction mixture under reduced pressure. The solid product obtained was filtered, washed with water and dried. Colorless needles of (I) were obtained from an ethanol solution by slow evaporation (Yield 53%), M.p. 488 K.

Computing details top

Data collection: APEX2 (Bruker, 2005); cell refinement: APEX2 (Bruker, 2005); data reduction: SAINT (Bruker, 2005); program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2003).

Figures top

	Fig. 1. The molecular structure of (I), showing 50% probability displacement ellipsoids for the non-hydrogen atoms. The N—H···O hydrogen bond is shown as a dashed line.
	Fig. 2. The packing diagram of (I), viewed along the a axis. Hydrogen bonds are shown as dashed lines.

4-Chloro-N'-[(Z)-4-nitrobenzylidene]benzohydrazide monohydrate top

Crystal data top

C₁₄H₁₀ClN₃O₃·H₂O	F(000) = 664
M_r = 321.72	D_x = 1.545 Mg m⁻³
Monoclinic, P2₁/c	Melting point: 488 K
Hall symbol: -P 2ybc	Mo Kα radiation, λ = 0.71073 Å
a = 16.3049 (8) Å	Cell parameters from 3172 reflections
b = 6.8783 (4) Å	θ = 1.3–27.5°
c = 12.7209 (7) Å	µ = 0.30 mm⁻¹
β = 104.122 (4)°	T = 100 K
V = 1383.53 (13) Å³	Needle, colorless
Z = 4	0.38 × 0.21 × 0.10 mm

Data collection top

Bruker SMART APEX2 CCD diffractometer	3172 independent reflections
Radiation source: fine-focus sealed tube	2558 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.044
Detector resolution: 8.33 pixels mm^-1	θ_max = 27.5°, θ_min = 1.3°
ω scans	h = −21→21
Absorption correction: multi-scan (SADABS; Bruker, 2005)	k = −7→8
T_min = 0.896, T_max = 0.971	l = −16→16
14031 measured reflections

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.086	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.239	H-atom parameters constrained
S = 1.13	w = 1/[σ²(F_o²) + (0.0417P)² + 15.1986P] where P = (F_o² + 2F_c²)/3
3172 reflections	(Δ/σ)_max < 0.001
199 parameters	Δρ_max = 1.40 e Å⁻³
0 restraints	Δρ_min = −0.46 e Å⁻³

Crystal data top

C₁₄H₁₀ClN₃O₃·H₂O	V = 1383.53 (13) Å³
M_r = 321.72	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 16.3049 (8) Å	µ = 0.30 mm⁻¹
b = 6.8783 (4) Å	T = 100 K
c = 12.7209 (7) Å	0.38 × 0.21 × 0.10 mm
β = 104.122 (4)°

Data collection top

Bruker SMART APEX2 CCD diffractometer	3172 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2005)	2558 reflections with I > 2σ(I)
T_min = 0.896, T_max = 0.971	R_int = 0.044
14031 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.086	0 restraints
wR(F²) = 0.239	H-atom parameters constrained
S = 1.13	w = 1/[σ²(F_o²) + (0.0417P)² + 15.1986P] where P = (F_o² + 2F_c²)/3
3172 reflections	Δρ_max = 1.40 e Å⁻³
199 parameters	Δρ_min = −0.46 e Å⁻³

Special details top

Experimental. The low-temperature data was collected with the Oxford Cyrosystem Cobra low-temperature attachment.

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Refinement. Refinement of F² against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The threshold expression of F² > σ(F²) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F² are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
Cl1	0.79974 (8)	0.8946 (2)	0.59885 (10)	0.0211 (3)
O1	−0.0852 (2)	0.7494 (7)	−0.1492 (3)	0.0312 (10)
O2	−0.0194 (2)	0.9231 (7)	−0.2447 (3)	0.0306 (10)
O3	0.5057 (2)	0.8432 (6)	0.1303 (3)	0.0167 (8)
N1	0.4189 (2)	0.8116 (6)	0.2433 (3)	0.0146 (8)
H1N1	0.4111	0.7946	0.3065	0.017*
N2	0.3494 (3)	0.8265 (6)	0.1565 (3)	0.0154 (9)
N3	−0.0222 (3)	0.8347 (7)	−0.1617 (3)	0.0196 (9)
C1	0.6514 (3)	0.8141 (8)	0.3030 (4)	0.0172 (10)
H1A	0.6578	0.7885	0.2336	0.021*
C2	0.7224 (3)	0.8303 (8)	0.3878 (4)	0.0184 (10)
H2A	0.7761	0.8149	0.3762	0.022*
C3	0.7118 (3)	0.8698 (8)	0.4901 (4)	0.0173 (10)
C4	0.6319 (3)	0.8910 (8)	0.5090 (4)	0.0173 (10)
H4A	0.6259	0.9173	0.5785	0.021*
C5	0.5614 (3)	0.8724 (8)	0.4236 (4)	0.0153 (10)
H5A	0.5077	0.8847	0.4359	0.018*
C6	0.5702 (3)	0.8354 (7)	0.3196 (4)	0.0143 (10)
C7	0.4969 (3)	0.8287 (7)	0.2234 (4)	0.0141 (9)
C8	0.2778 (3)	0.7923 (8)	0.1770 (4)	0.0166 (10)
H8A	0.2749	0.7564	0.2465	0.020*
C9	0.2003 (3)	0.8100 (8)	0.0902 (4)	0.0152 (10)
C10	0.1241 (3)	0.7367 (8)	0.1067 (4)	0.0181 (11)
H10A	0.1230	0.6841	0.1737	0.022*
C11	0.0507 (3)	0.7417 (8)	0.0248 (4)	0.0193 (11)
H11A	0.0005	0.6890	0.0346	0.023*
C12	0.0543 (3)	0.8281 (8)	−0.0724 (4)	0.0171 (10)
C13	0.1275 (3)	0.9111 (8)	−0.0900 (4)	0.0165 (10)
H13A	0.1272	0.9735	−0.1549	0.020*
C14	0.2009 (3)	0.8985 (8)	−0.0080 (4)	0.0168 (10)
H14A	0.2510	0.9496	−0.0187	0.020*
O1W	0.3845 (2)	0.6173 (6)	0.4228 (3)	0.0196 (8)
H1W	0.4181	0.5223	0.4141	0.029*
H2W	0.3862	0.6256	0.4931	0.029*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cl1	0.0164 (6)	0.0226 (7)	0.0194 (6)	−0.0002 (5)	−0.0049 (4)	−0.0009 (5)
O1	0.0116 (17)	0.049 (3)	0.032 (2)	−0.0057 (18)	0.0034 (15)	0.003 (2)
O2	0.022 (2)	0.046 (3)	0.0199 (19)	−0.0012 (19)	−0.0013 (15)	0.0072 (19)
O3	0.0168 (16)	0.023 (2)	0.0106 (15)	−0.0028 (15)	0.0035 (12)	−0.0020 (14)
N1	0.0144 (19)	0.019 (2)	0.0097 (17)	−0.0017 (17)	0.0010 (14)	−0.0001 (17)
N2	0.0141 (19)	0.015 (2)	0.0153 (19)	−0.0017 (16)	−0.0010 (15)	−0.0012 (17)
N3	0.0113 (19)	0.027 (3)	0.019 (2)	0.0000 (18)	0.0008 (16)	0.0010 (19)
C1	0.020 (2)	0.018 (3)	0.015 (2)	0.001 (2)	0.0050 (18)	0.000 (2)
C2	0.014 (2)	0.019 (3)	0.022 (2)	0.001 (2)	0.0038 (19)	0.000 (2)
C3	0.016 (2)	0.015 (3)	0.017 (2)	−0.0024 (19)	−0.0034 (18)	0.002 (2)
C4	0.020 (2)	0.018 (3)	0.013 (2)	−0.001 (2)	0.0028 (18)	−0.001 (2)
C5	0.016 (2)	0.016 (2)	0.015 (2)	0.0005 (19)	0.0049 (17)	−0.0023 (19)
C6	0.015 (2)	0.011 (2)	0.016 (2)	−0.0011 (18)	0.0024 (17)	−0.0006 (19)
C7	0.013 (2)	0.011 (2)	0.018 (2)	0.0008 (18)	0.0025 (18)	−0.0003 (19)
C8	0.018 (2)	0.019 (3)	0.012 (2)	0.000 (2)	0.0015 (18)	0.000 (2)
C9	0.013 (2)	0.016 (2)	0.015 (2)	−0.0001 (19)	0.0026 (17)	−0.001 (2)
C10	0.017 (2)	0.023 (3)	0.015 (2)	0.000 (2)	0.0055 (18)	0.005 (2)
C11	0.014 (2)	0.022 (3)	0.022 (2)	−0.001 (2)	0.0044 (19)	0.003 (2)
C12	0.013 (2)	0.022 (3)	0.015 (2)	0.003 (2)	0.0000 (17)	0.001 (2)
C13	0.015 (2)	0.019 (3)	0.014 (2)	−0.001 (2)	0.0030 (18)	0.000 (2)
C14	0.013 (2)	0.019 (3)	0.018 (2)	0.0011 (19)	0.0031 (18)	−0.001 (2)
O1W	0.0201 (17)	0.028 (2)	0.0111 (15)	0.0008 (16)	0.0047 (13)	−0.0007 (15)

Geometric parameters (Å, º) top

Cl1—C3	1.741 (5)	C5—C6	1.389 (7)
O1—N3	1.226 (6)	C5—H5A	0.9300
O2—N3	1.228 (6)	C6—C7	1.488 (6)
O3—C7	1.232 (6)	C8—C9	1.466 (6)
N1—C7	1.361 (6)	C8—H8A	0.9300
N1—N2	1.379 (5)	C9—C14	1.391 (7)
N1—H1N1	0.8525	C9—C10	1.404 (7)
N2—C8	1.279 (6)	C10—C11	1.383 (7)
N3—C12	1.469 (6)	C10—H10A	0.9300
C1—C2	1.380 (7)	C11—C12	1.387 (7)
C1—C6	1.399 (7)	C11—H11A	0.9300
C1—H1A	0.9300	C12—C13	1.390 (7)
C2—C3	1.382 (7)	C13—C14	1.384 (7)
C2—H2A	0.9300	C13—H13A	0.9300
C3—C4	1.388 (7)	C14—H14A	0.9300
C4—C5	1.381 (6)	O1W—H1W	0.8771
C4—H4A	0.9300	O1W—H2W	0.8898

C7—N1—N2	117.9 (4)	O3—C7—N1	121.2 (4)
C7—N1—H1N1	123.2	O3—C7—C6	122.0 (4)
N2—N1—H1N1	118.9	N1—C7—C6	116.8 (4)
C8—N2—N1	115.9 (4)	N2—C8—C9	119.6 (4)
O1—N3—O2	123.8 (4)	N2—C8—H8A	120.2
O1—N3—C12	117.7 (4)	C9—C8—H8A	120.2
O2—N3—C12	118.5 (4)	C14—C9—C10	119.4 (4)
C2—C1—C6	121.2 (5)	C14—C9—C8	121.3 (4)
C2—C1—H1A	119.4	C10—C9—C8	119.3 (4)
C6—C1—H1A	119.4	C11—C10—C9	120.9 (5)
C1—C2—C3	118.6 (5)	C11—C10—H10A	119.6
C1—C2—H2A	120.7	C9—C10—H10A	119.6
C3—C2—H2A	120.7	C10—C11—C12	117.7 (5)
C2—C3—C4	121.4 (4)	C10—C11—H11A	121.1
C2—C3—Cl1	120.0 (4)	C12—C11—H11A	121.1
C4—C3—Cl1	118.6 (4)	C11—C12—C13	123.0 (4)
C5—C4—C3	119.3 (5)	C11—C12—N3	119.3 (4)
C5—C4—H4A	120.3	C13—C12—N3	117.7 (4)
C3—C4—H4A	120.3	C14—C13—C12	118.1 (5)
C4—C5—C6	120.4 (5)	C14—C13—H13A	120.9
C4—C5—H5A	119.8	C12—C13—H13A	120.9
C6—C5—H5A	119.8	C13—C14—C9	120.6 (5)
C5—C6—C1	119.0 (4)	C13—C14—H14A	119.7
C5—C6—C7	122.7 (4)	C9—C14—H14A	119.7
C1—C6—C7	118.2 (4)	H1W—O1W—H2W	107.9

C7—N1—N2—C8	174.0 (5)	N1—N2—C8—C9	178.3 (4)
C6—C1—C2—C3	−0.5 (8)	N2—C8—C9—C14	−12.5 (8)
C1—C2—C3—C4	0.8 (8)	N2—C8—C9—C10	167.7 (5)
C1—C2—C3—Cl1	−179.2 (4)	C14—C9—C10—C11	3.6 (8)
C2—C3—C4—C5	−0.1 (8)	C8—C9—C10—C11	−176.7 (5)
Cl1—C3—C4—C5	179.8 (4)	C9—C10—C11—C12	−2.4 (8)
C3—C4—C5—C6	−0.8 (8)	C10—C11—C12—C13	−1.0 (8)
C4—C5—C6—C1	1.1 (8)	C10—C11—C12—N3	179.5 (5)
C4—C5—C6—C7	−175.3 (5)	O1—N3—C12—C11	−5.5 (8)
C2—C1—C6—C5	−0.4 (8)	O2—N3—C12—C11	175.2 (5)
C2—C1—C6—C7	176.2 (5)	O1—N3—C12—C13	174.9 (5)
N2—N1—C7—O3	−5.1 (7)	O2—N3—C12—C13	−4.4 (8)
N2—N1—C7—C6	173.0 (4)	C11—C12—C13—C14	3.1 (8)
C5—C6—C7—O3	162.0 (5)	N3—C12—C13—C14	−177.3 (5)
C1—C6—C7—O3	−14.4 (8)	C12—C13—C14—C9	−1.9 (8)
C5—C6—C7—N1	−16.1 (7)	C10—C9—C14—C13	−1.3 (8)
C1—C6—C7—N1	167.5 (5)	C8—C9—C14—C13	178.9 (5)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1W—H1W···O3ⁱ	0.88	1.93	2.794 (5)	168
O1W—H2W···O3ⁱⁱ	0.89	2.29	2.898 (5)	126
O1W—H2W···N2ⁱⁱ	0.89	2.32	3.185 (5)	163
N1—H1N1···O1W	0.85	2.04	2.818 (5)	151
C2—H2A···O1ⁱⁱⁱ	0.93	2.40	3.329 (6)	176
C14—H14A···O1W^iv	0.93	2.51	3.322 (6)	146

Symmetry codes: (i) −x+1, y−1/2, −z+1/2; (ii) x, −y+3/2, z+1/2; (iii) x+1, −y+3/2, z+1/2; (iv) x, −y+3/2, z−1/2.

Experimental details

Crystal data
Chemical formula	C₁₄H₁₀ClN₃O₃·H₂O
M_r	321.72
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	100
a, b, c (Å)	16.3049 (8), 6.8783 (4), 12.7209 (7)
β (°)	104.122 (4)
V (Å³)	1383.53 (13)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.30
Crystal size (mm)	0.38 × 0.21 × 0.10

Data collection
Diffractometer	Bruker SMART APEX2 CCD diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2005)
T_min, T_max	0.896, 0.971
No. of measured, independent and observed [I > 2σ(I)] reflections	14031, 3172, 2558
R_int	0.044
(sin θ/λ)_max (Å⁻¹)	0.650

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.086, 0.239, 1.13
No. of reflections	3172
No. of parameters	199
H-atom treatment	H-atom parameters constrained
	w = 1/[σ²(F_o²) + (0.0417P)² + 15.1986P] where P = (F_o² + 2F_c²)/3
Δρ_max, Δρ_min (e Å⁻³)	1.40, −0.46

Computer programs: APEX2 (Bruker, 2005), SAINT (Bruker, 2005), SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2003).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1W—H1W···O3ⁱ	0.88	1.93	2.794 (5)	168
O1W—H2W···O3ⁱⁱ	0.89	2.29	2.898 (5)	126
O1W—H2W···N2ⁱⁱ	0.89	2.32	3.185 (5)	163
N1—H1N1···O1W	0.85	2.04	2.818 (5)	151
C2—H2A···O1ⁱⁱⁱ	0.93	2.40	3.329 (6)	176
C14—H14A···O1W^iv	0.93	2.51	3.322 (6)	146

Symmetry codes: (i) −x+1, y−1/2, −z+1/2; (ii) x, −y+3/2, z+1/2; (iii) x+1, −y+3/2, z+1/2; (iv) x, −y+3/2, z−1/2.

Footnotes

‡Additional correspondence author, e-mail: suchada.c@psu.ac.th.

Acknowledgements

JNR and BK are grateful to Kerala State Council for Science Technology and Environment, Thiruvananthapuram, for financial assistance. The authors also thank Universiti Sains Malaysia for the Research University Golden Goose grant No. 1001/PFIZIK/811012.

References

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